Connected by a granite causeway to the mainland at Pleasant Point Reservation, Eastport has wonderful views of the nearby islands, and because the harbor is so deep, you can sometimes spot whales from the waterfront. Known for its diverse architecture, the island city was one of the nation's busiest seaports in the early 1800s.
If you find yourself in town mid- to late summer, you might catch one of a few notable events. For starters, Maine's largest Fourth of July parade takes place in Eastport—be sure to get downtown early to secure a viewing spot. Then, on the weekend of the second Sunday in August, locals celebrate Sipayik Indian Days at the Pleasant Point Reservation; this festival of Passamaquoddy culture includes canoe races, dancing, drumming, children's games, fireworks, and traditional dancing. And on the weekend after Labor Day, the Eastport Pirate Festival brings folks out in pirate attire for a ship race, a parade, fireworks, cutlass "battles" by reenactors, and other events, including a children's breakfast and a schooner ride with pirates.